A beach with people standing and facing the ocean, with their arms raised. There are two suitcases on the sand.

Find Hotels with a Pool in Holiday, FL

  • Upfront pricing

    Our total price for your stay includes taxes and fees

  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check availability on Holiday Hotels with a Pool

Tonight
Oct 15 - Oct 16
Tomorrow
Oct 16 - Oct 17
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

Our top choices for Holiday hotels with a pool

A swimming pool with a no diving sign, lounge chairs, and a lifeguard on duty sign.
A hotel dining area with multiple tables and chairs, a counter with food and beverage options, and large windows providing natural light.
Room
A lobby with a reception desk, green upholstered seating, a white coffee table, and a blue patterned rug.

1. Fairfield Inn & Suites Holiday Tarpon Springs

Fairfield Inn & Suites Holiday Tarpon Springs
Holiday
  • Dive into poolside paradise with premium loungers and sun-dappled waters at this serene hotel retreat.
$107 nightly
$120 total
Oct 20 - Oct 21
Total with taxes and fees
Fairfield Inn & Suites Holiday Tarpon Springs
A backyard with a swimming pool, lounge chairs, and a patio area.
A modern living room with a flat-screen TV, a dining area with chairs, and a large window.
A modern living room with a blue sofa, a flat-screen TV mounted on the wall, and a decorative vase with dried flowers.
A bedroom with a bed, a bedside table, a TV mounted on the wall, and a window with curtains.

2. Sunny Oasis by Tarpon - Heated Pool, Hot Tub & Playground

Sunny Oasis by Tarpon - Heated Pool, Hot Tub & Playground
Holiday
$238 nightly
$263 total
Nov 1 - Nov 2
Total with taxes and fees
Sunny Oasis by Tarpon - Heated Pool, Hot Tub & Playground
A poolside view with a glass of drink, a covered seating area, and a view of the sunset over a body of water.
A modern living room with a sectional sofa, a small round table, and a bar area with stools.
A fire pit with two Adirondack chairs, a stone fire surround, and a view of a body of water with lights in the background.
An aerial view of a residential area with a swimming pool, a dock, and a well-maintained lawn.

3. Lakefront Paradise, with Heated Private Pool.

Lakefront Paradise, with Heated Private Pool.
Tahitian Development
  • Lakefront paradise offers families private pool enjoyment while viewing wildlife from the water.
$368 nightly
$407 total
Oct 18 - Oct 19
Total with taxes and fees
Lakefront Paradise, with Heated Private Pool.
A rectangular swimming pool with clear blue water, surrounded by a black fence.
A lifeguard tower with a flat roof, multiple windows, and a metal railing.
A beach with umbrellas, beach chairs, and people swimming in the water.
A hammock on a wooden deck overlooking a lake with houses in the background.

4. GREAT LOCATION WATERFRONT, HEATED POOL! BEAUTIFUL SUNSETS, ALL PETS STAY FREE!

GREAT LOCATION WATERFRONT, HEATED POOL! BEAUTIFUL SUNSETS, ALL PETS STAY FREE!
Holiday
$479 nightly
$530 total
Oct 16 - Oct 17
Total with taxes and fees
GREAT LOCATION WATERFRONT, HEATED POOL! BEAUTIFUL SUNSETS, ALL PETS STAY FREE!
A covered outdoor swimming pool with a slide, lounge chairs, and a patio area.
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.
A modern kitchen with white cabinets, a central island with bar stools, a ceiling fan, pendant lights, and a large window with blinds.
A modern kitchen with white cabinets, a central island, and a dining area with a table and chairs.

5. Coastal Family Retreat – Heated Pool, Fire Pit & Fun!

Coastal Family Retreat – Heated Pool, Fire Pit & Fun!
Holiday Lakes West
$413 nightly
$457 total
Oct 21 - Oct 22
Total with taxes and fees
Coastal Family Retreat – Heated Pool, Fire Pit & Fun!
A house with a swimming pool, outdoor seating, and a piano.
A modern kitchen with stainless steel appliances, light-colored cabinetry, and a central island.
A beach with white sand, palm trees, and a pier in the background.
A backyard with a swimming pool, outdoor seating, and a barbecue area.

6. Coastal Family Escape with Heated Private Pool•Near Beaches

Coastal Family Escape with Heated Private Pool•Near Beaches
Holiday
$434 nightly
$479 total
Oct 18 - Oct 19
Total with taxes and fees
Coastal Family Escape with Heated Private Pool•Near Beaches
A covered outdoor seating area with a pool in the background.
A kitchen with granite countertops, a stainless steel sink, and a coffee station.
A modern kitchen with white cabinets, a granite countertop, and a built-in microwave. There are two brown chairs and a small table with decorative items.
A dining area with a dark wooden table set for six, surrounded by brown leather chairs.

7. Luxe Retreat with Resort-Style Backyard w/Heated Pool • Fire Pit • Near Beaches

Luxe Retreat with Resort-Style Backyard w/Heated Pool • Fire Pit • Near Beaches
Holiday
$445 nightly
$491 total
Oct 18 - Oct 19
Total with taxes and fees
Luxe Retreat with Resort-Style Backyard w/Heated Pool • Fire Pit • Near Beaches
A swimming pool with a glass enclosure, outdoor seating, and a white building with large windows.
A spacious living room with a grey sectional sofa, a small round table, and a flat-screen TV.
A modern kitchen with white cabinetry, stainless steel appliances, and a coffee maker.
A dining area with a table and chairs, large windows, and a view of a swimming pool.

8. Cozy Canal-Front Getaway•Heated Pool•Relaxation•Fishing•Beaches Nearby

Cozy Canal-Front Getaway•Heated Pool•Relaxation•Fishing•Beaches Nearby
Holiday Lake Estates
$458 nightly
$505 total
Nov 2 - Nov 3
Total with taxes and fees
Cozy Canal-Front Getaway•Heated Pool•Relaxation•Fishing•Beaches Nearby
A hotel with a swimming pool, outdoor seating, and palm trees.
A hotel room with a bed, a desk with a television, a chair, a nightstand with a lamp, and a view of the outdoors through the window.
A covered outdoor seating area with a pool, lounge chairs, and a table.
A bar area with wooden chairs, a counter with bottles, and a TV mounted on the wall.

9. Quality Inn & Suites Tarpon Springs South

Quality Inn & Suites Tarpon Springs South
Tarpon Springs
  • Soak up the sun at this tranquil hotel pool retreat with comfortable lounge chairs and beautiful landscaped gardens.
$80 nightly
$91 total
Oct 22 - Oct 23
Total with taxes and fees
Quality Inn & Suites Tarpon Springs South
A swimming pool with a tiled deck, a building with a blue facade, and a clear sky.
A modern reception area with a wooden panel wall, a crescent moon design, and a counter with computers.
A modern hotel with a prominent 'Comfort Inn & Suites' sign, a well-lit entrance, and a landscaped area with a small pool.
A modern kitchen with a central island, a dining area with yellow chairs, and a living space with a blue sofa.

10. Comfort Inn & Suites New Port Richey Downtown District

Comfort Inn & Suites New Port Richey Downtown District
New Port Richey
  • Escape to a sparkling oasis at this downtown hotel with a refreshing outdoor pool experience.
$86 nightly
$97 total
Nov 1 - Nov 2
Total with taxes and fees
Comfort Inn & Suites New Port Richey Downtown District
View all properties

Choose what matters most at hotels with a pool in Holiday

Breakfast included
Hot tub
4 stars
5 stars
Spa

Top Holiday Hotel Reviews

DoubleTree by Hilton Tampa Rocky Point Waterfront

DoubleTree by Hilton Tampa Rocky Point Waterfront

10/10 Excellent
"wonderful very clean great staff and great restaurant"
Cynthia 1-night trip
Posted 1 hour ago
DoubleTree by Hilton Tampa Rocky Point Waterfront
Fairfield Inn & Suites by Marriott Clearwater Beach

Fairfield Inn & Suites by Marriott Clearwater Beach

10/10 Excellent
"The location is great. Walkable or they provided a golfcart shuttle to the beach 4 blocks away. They will also shuttle you to nearby restaurants. Friendly helpful staff. Only downfall is we upgraded to a water view room and the view was just a sliver out the window."
LISA 1-night trip
Posted 11 hours ago
Fairfield Inn & Suites by Marriott Clearwater Beach
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

8/10 Good
"Very clean and good service"
David 5-night trip
Posted 15 hours ago
Wyndham Grand Clearwater Beach
Gulfview Hotel on the Beach

Gulfview Hotel on the Beach

8/10 Good
"Nice private beach. Need to have chairs and umbrellas on the beach"
Dennis 3-night trip
Posted 19 hours ago
Gulfview Hotel on the Beach
Grand Hyatt Tampa Bay

Grand Hyatt Tampa Bay

10/10 Excellent
"The restaurant and lounge was great."
anthony 3-night trip
Posted 23 hours ago
Grand Hyatt Tampa Bay
Opal Sands Resort

Opal Sands Resort

10/10 Excellent
"Best"
Daniela 2-night trip
Posted 2 days ago
Opal Sands Resort
Pelican Pointe Clearwater Beach Hotel

Pelican Pointe Clearwater Beach Hotel

10/10 Excellent
"We had an adventure. Our original hotel had a fire and we were forced to find different accommodations that evening. Our hostess found us a room at your hotel and took care us. We enjoyed the hot tub, pool and beach area. It was great. Thank you again for taking such great care of us."
Anonymous traveler 2-night trip
Posted 2 days ago
Pelican Pointe Clearwater Beach Hotel

Frequently asked questions

What are the best hotels in Holiday with outdoor pools?
The Fairfield Inn & Suites Holiday Tarpon Springs is a fantastic option for travellers seeking a hotel with an inviting outdoor pool. Rated 9.0 by guests, this hotel stands out not only for its refreshing pool but also for the complimentary continental breakfast that many have described as excellent and tasty.Families will appreciate the extra conveniences, such as free WiFi and self-parking, allowing for a straightforward stay. The attentive staff has received high praise, often being described as great and amazing, ensuring an inviting space for both parents and children.
How much does a hotel with outdoor pool in Holiday cost?
Enjoy staying in a hotel in Holiday with an outdoor pool. You can find a great deal from $97 on Expedia. If you're leaning toward a little luxury, prices can rise, and may vary depending on the location, season, and hotel amenities. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during weekends or around public holidays.
Is it cheaper to book flights and a Holiday hotel with a pool as a package?
Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect vacation package.
Can I cancel my hotel reservation on Expedia?
Expedia has plenty of refundable hotels. In many cases, you need to cancel your booking 24-48 hours ahead of your arrival date. Remember to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right hotel in Holiday for you.

Explore a world of travel with Expedia